Diethylthiambutene

Diethylthiambutene
Clinical data
ATC code	none;
Legal status
Legal status	BR: Class A1 (Narcotic drugs); CA: Schedule I; DE: Anlage I (Authorized scientific use only); US: Schedule I; UN: Psychotropic Schedule I;
Identifiers
	IUPAC name N,N-diethyl-4,4-dithiophen-2-yl-but-3-en-2-amine;
CAS Number	86-14-6 ;
PubChem CID	6833;
DrugBank	DB01533 ;
ChemSpider	6572 ;
UNII	2Z91X9052O;
KEGG	D12664 ;
ChEMBL	ChEMBL2106573 ;
CompTox Dashboard (EPA)	DTXSID30861666 ;
Chemical and physical data
Formula	C16H21NS2
Molar mass	291.47 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	152 to 153 °C (306 to 307 °F)
	SMILES CCN(CC)C(C)C=C(C1=CC=CS1)C2=CC=CS2;
	InChI InChI=1S/C16H21NS2/c1-4-17(5-2)13(3)12-14(15-8-6-10-18-15)16-9-7-11-19-16/h6-13H,4-5H2,1-3H3 ; Key:CBYWMRHUUVRIAF-UHFFFAOYSA-N ;
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Diethylthiambutene (Thiambutene, Themalon, Diethibutin, N,N-Diethyl-1-methyl-3,3-di-2-thienylallylamine) is an opioid analgesic drug developed in the 1950s^[2] which was mainly used as an anesthetic in veterinary medicine and continues, along with the other two thiambutenes dimethylthiambutene and ethylmethylthiambutene to be used for this purpose, particularly in Japan.^[3]^[4] It is now under international control under Schedule I of the UN Single Convention On Narcotic Drugs 1961, presumably due to high abuse potential, although little more information is available. It is listed under Schedule I of the US Controlled Substances Act as a Narcotic and has an ACSCN of 9616 with zero annual manufacturing quota as of 2013.

Synthesis

Synthesis:^[5] Japan patents:^[6]

The conjugate addition of diethylamine [109-89-7] to ethyl crotonate [623-70-1] [10544-63-5] (1) gives ethyl 3-(diethylamino)butanoate, CID:10679145 (2). Addition of two equivalents of 2-thienyllithium to the ester gives the tertiary alcohol [94094-46-9] (4'). The dehydration of this then completes the synthesis of diethylthiambutene (5').

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Beckett AH, Casy AF, Harper NJ, Phillips PM (November 1956). "Analgesics and their antagonists: some steric and chemical considerations. II. The influence of the basic group on physico-chemical properties and the activity of methadone and thiambutene-type compounds". The Journal of Pharmacy and Pharmacology. 8 (11): 860–73. doi:10.1111/j.2042-7158.1956.tb12216.x. PMID 13368083. S2CID 41750428.
^ Hayes MJ (November 1968). "The use of thiambutene hydrochloride". The Veterinary Record. 83 (20): 528. doi:10.1136/vr.83.20.528-a. PMID 5694027. S2CID 45820838.
^ Harbison WD, Slocombe RF, Watts SJ, Stewart GA (December 1974). "Thiambutene and acepromazine as analgesic and preanaesthetic agents in horses and sheep". Australian Veterinary Journal. 50 (12): 543–6. doi:10.1111/j.1751-0813.1974.tb14073.x. PMID 4156466.
^ Adamson, D. W. (1950). "180. Aminoalkyl tertiary carbinols and derived products. Part II. 3-Amino-1 : 1-di-2′-thienyl-alkan-1-ols and -alk-1-enes". J. Chem. Soc. 0 (0): 885–890. doi:10.1039/JR9500000885.
^ JP,43-006621,B (1968) JP,0528324,B

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[1] Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.

[pmid13368083-2] Beckett AH, Casy AF, Harper NJ, Phillips PM (November 1956). "Analgesics and their antagonists: some steric and chemical considerations. II. The influence of the basic group on physico-chemical properties and the activity of methadone and thiambutene-type compounds". The Journal of Pharmacy and Pharmacology. 8 (11): 860–73. doi:10.1111/j.2042-7158.1956.tb12216.x. PMID 13368083. S2CID 41750428.

[pmid5694027-3] Hayes MJ (November 1968). "The use of thiambutene hydrochloride". The Veterinary Record. 83 (20): 528. doi:10.1136/vr.83.20.528-a. PMID 5694027. S2CID 45820838.

[pmid4156466-4] Harbison WD, Slocombe RF, Watts SJ, Stewart GA (December 1974). "Thiambutene and acepromazine as analgesic and preanaesthetic agents in horses and sheep". Australian Veterinary Journal. 50 (12): 543–6. doi:10.1111/j.1751-0813.1974.tb14073.x. PMID 4156466.

[5] Adamson, D. W. (1950). "180. Aminoalkyl tertiary carbinols and derived products. Part II. 3-Amino-1 : 1-di-2′-thienyl-alkan-1-ols and -alk-1-enes". J. Chem. Soc. 0 (0): 885–890. doi:10.1039/JR9500000885.

[6] JP,43-006621,B (1968) JP,0528324,B

[2]

[3]

[4]

[1]

[5]

[6]

Clinical data

ATC code	none
Legal status
Legal status	BR: Class A1 (Narcotic drugs)^[1] CA: Schedule I DE: Anlage I (Authorized scientific use only) US: Schedule I UN: Psychotropic Schedule I
Identifiers
IUPAC name N,N-diethyl-4,4-dithiophen-2-yl-but-3-en-2-amine
CAS Number	86-14-6^N
PubChem CID	6833
DrugBank	DB01533^Y
ChemSpider	6572^Y
UNII	2Z91X9052O
KEGG	D12664^Y
ChEMBL	ChEMBL2106573^N
CompTox Dashboard (EPA)	DTXSID30861666
Chemical and physical data
Formula	C₁₆H₂₁NS₂
Molar mass	291.47 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	152 to 153 °C (306 to 307 °F)
SMILES CCN(CC)C(C)C=C(C1=CC=CS1)C2=CC=CS2
InChI InChI=1S/C16H21NS2/c1-4-17(5-2)13(3)12-14(15-8-6-10-18-15)16-9-7-11-19-16/h6-13H,4-5H2,1-3H3^Y Key:CBYWMRHUUVRIAF-UHFFFAOYSA-N^Y
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